How Saving Private Ryan’s Best Picture Loss Changed the Oscars Forever

More than just an upset, Saving Private Ryan losing the Best Picture Oscar to Shakespeare in Love changed how Academy Awards are won.

Tom Hanks and Tom Sizemore in D-Day boat in Saving Private Ryan
Photo: DreamWorks Pictures

Saving Private Ryan’s loss of the Best Picture Oscar in 1999 still hurts. It’s a sentiment shared by many, and not just because of the disappointment they experienced when Shakespeare in Love took home that night’s top prize. After all, there have been plenty of upsets before and since. Just ask Brokeback Mountain’s producers about Crash, or La La Land’s about Moonlight. If Orson Welles was still alive, the stories he’d surely have to tell about How Green is My Valley.

Yet when it comes to Steven Spielberg’s seminal World War II epic losing to an amusing (if somewhat lightweight) romantic comedy, never before had there been an upset so fundamentally unexpected that it changed the way awards were won; and never before had a generally celebrated studio hit with frontrunner status run into the political machinations of Harvey Weinstein. The Oscars would never be the same.

Released in July 1998, Saving Private Ryan opened during a peak of renewed interest in the generation of Americans who endured the Great Depression and then won World War II, transforming the U.S. into a superpower. Later in the same year as Saving Private Ryan, Tom Brokaw’s book The Greatest Generation would popularize the term used by its title to describe their sacrifice. But by the time that was published, Spielberg had already given the idea visual form for younger audiences.

With an intense commitment to realism and authenticity, the director’s use of shaky handheld photography and brutally unsentimental depictions of violence were shocking in 1998. The opening sequence, centered on the D-Day landing, especially evoked documentary filmmaking, creating horror so visceral it would soon change the way war movies were shot. In that specific moment, however, all this suffering made the sacrifice of the film’s heroes—eight American soldiers sent behind enemy lines to bring one paratrooper home—appear Herculean.

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The film was a massive blockbuster hit, back when $482 million worldwide was considered massive and blockbusters could be about more than superheroes and space wizards. Going forward there was little doubt in most conventional Oscar watchers’ minds that Spielberg had his second Best Picture Oscar sewn up.

Come Oscar night though, Spielberg picked up the Best Director Oscar (his second after Schindler’s List) while John Madden’s Shakespeare in Love left audiences at home surprised by taking the top award, alongside its wins for Best Actress, Best Supporting Actress, Best Original Screenplay, and Best Score… the latter two also at Saving Private Ryan’s expense.

Unto itself Shakespeare in Love is a charming film, essentially a backstage dramedy with literary pedigree. Ostensibly a fictionalized origin story for how the Bard got the idea for Romeo and Juliet, the film inserts insider Hollywood humor into an Elizabethan setting while also offering a lush romance between old Will and his personal Juliet (or Twelfth Night’s Violet, depending on the scene). It can be a sweet movie, but until 1998, it was not the kind of film that won Best Picture. In fact, most of the biggest winners of the ‘90s had been widely popular studio blockbusters: Titanic dubiously beat L.A. Confidential the year before; Braveheart beat Sense and Sensibility in 1996; and the year prior to that saw Forrest Gump defeat the Quentin Tarantino trailblazer, Pulp Fiction.

That latter case of popularity beating indie credibility was perhaps the most important to 1999, since that year’s conventional, feel-good Tom Hanks vehicle not only beat out a critical darling, but it beat a film produced by Miramax Films, a then-speciality arm of Disney which was originally founded (and still run) as an indie distributor by Bob and Harvey Weinstein. You likely know the latter’s name.

Before Harvey Weinstein became the notoriously disgraced figure of our post-#MeToo era—which culminated with his sentence to 23 years in prison after being convicted on one count of sexual assault in the first degree and one count of rape in the third degree—he reigned in Hollywood with impunity. And his throne room was the Oscar stage. Unlike other studios, Weinstein’s made the accruement of Oscars the centerpiece of its release strategy, building prestige and attention off award wins, and transforming that into belated box office dollars. The process redefined what an “Oscar Movie” looked like: they generally became smaller budgeted, less seen, and often greenlit with (if not written for) Academy voters’ preconceived tastes in mind.

Shakespeare in Love beating Saving Private Ryan was the turning point that implemented this sea change.

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When the Weinstein-produced comedy first screened for Academy voters in December 1998, the movie was met by a reportedly cool reception, signaling the film would have a small impact on the year’s Oscar race. However, as detailed by Rebecca Keegan and Nicole Sperling’s intricate reporting in Vanity Fair, Weinstein’s pioneering Oscar campaign for that movie would become his “bully masterpiece.”

Prior to Shakespeare in Love’s win, Oscar campaigns were generally a cordial, good old boys affair. There would be industry screenings for Academy voters and the guilds, of course, and promotions in trade newspapers that would provide “For Your Consideration” pullout ads. However, Weinstein more or less invented the relentless months-long Oscar campaign that ends in February, but can begin as early as September.

Previously, promoting a movie for a filmmaker or actor might include appearing on talk shows ahead of the week of release, and doing a weekend of junket interviews. But after Shakespeare in Love, if a film had Oscar prospects it became an almost weekly obligation of appearing at screenings, participating in countless Q&As, and glad-handing at parties with awards voters. In fact, Academy voters got in trouble in ’98 for attending Weinstein’s “Welcome to America” party at New York’s posh Elaine’s restaurant—it was in honor of British Shakespeare in Love director, John Madden.

“It all began with Harvey,” one publicist told Vanity Fair. “I don’t remember ever feeling pressure like that from other studios. He was like, ‘Can you do these radio call-ins all morning?’ He calls the clients directly and guilts them. He really is a beast.”

Former Miramax executive Mark Gill described it as if the movie’s release was only an opening salvo for the publicity requirements placed on actors at the studio. “That was just ‘Good morning,’” said Gill. “You’ve got three months of shaking hands and kissing babies in you.”

Back in 1999, there was of course some resistance to this style of aggressively brazen schmoozing. Chief among the skeptics was Spielberg, the director of Saving Private Ryan and a Hollywood legend who didn’t feel the need to essentially beg for trophies.

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“I said [to Steven Spielberg], ‘Listen, this is what’s going on,’” recalled Terry Press, a marketer then working at Spielberg’s DreamWorks Pictures. “Steven said to me, ‘I do not want to get down in the mud with Harvey.’”

TCM host Ben Mankiewicz also recalled these events when Den of Geek spoke with him several years ago.

Said Mankiewicz, “Spielberg was urged to counter… and Spielberg being a normal, well-adjusted good person who believed in the process [said] ‘No, I’m not going to campaign for my movie. I’ll do promotions for my movie, but I’m not going to try and charm people and send them things so they vote for my movie.’”

Meanwhile Miramax started a whisper campaign saying everything good about Saving Private Ryan occurred within the first 15-20 minutes on the beaches of Normandy, and the rest was sentimental hokum. It worked. Spielberg did not campaign like it’s the Monday before election day, and Weinstein did.

While Weinstein is thankfully gone, the crude lessons learned by Shakespeare in Love’s win over Saving Private Ryan are not. Awards seasons generally begin in early September with the Venice Film Festival and the Toronto International Film Festival acting as unofficial clearinghouses for studios and distributors to showcase their most award-friendly wares. It then continues with each film being released between October and December, mounting months-long rollouts that never really end until Oscar night.

Coupled with corporate studio interests leaning evermore heavily on “four-quadrant” blockbusters that are built on franchises, this system has created an environment where Oscar movies are often little-seen limited releases, and mainstream populist films are more concerned with superpowers than prestige. While the actual type of movies nominated for Best Picture appear to be gradually changing—from more diversity among the winners like Moonlight and Parasite to even superhero movies like Black Panther and Joker now getting nods—the generally accepted wisdom that Oscar movies and popular movies are mutually exclusive remains intact.

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In other words, the studios rarely make movies like Saving Private Ryan anymore, and what is making big money is not the type of film to end up on “Best of the Year” lists come December. But even when there are exceptions to the rule, and studios let auteurs make a Dunkirk or a 1917, the filmmakers will still be spending months in what Spielberg once called “the mud.”

“It ranks pretty low in the list of lousy things that Harvey Weinstein did, they’re terrible what Harvey Weinstein did,” Mankiewicz told us. “But it’s on the list.”